Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR2614)
Drug Name
Beta-ionone
Synonyms
BETA-IONONE; beta-Cyclocitrylideneacetone; beta-E-Ionone; trans-beta-Ionone; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (E)-beta-Ionone; .beta.-Ionone; 14901-07-6; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-; 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one; 4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 79-77-6; NSC 402758; UNII-A7NRR1HLH6
Indication Breast cancer [ICD11: 2C60] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 192.3 Topological Polar Surface Area 17.1
Heavy Atom Count 14 Rotatable Bond Count 2
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
638014
ChEBI ID
CHEBI:32325
CAS Number
79-77-6
Formula
C13H20O
Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=O)C
InChI
1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
InChIKey
PSQYTAPXSHCGMF-BQYQJAHWSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
(+)-(S)-4-hydroxy--ionone DM006939
13854911
Oxidation - 4S-hydroxylation 1 [7]
(?)-(R)-4-hydroxy--ionones DM006941
10954777
Oxidation - 4-hydroxylation 1 [7]
3-hydroxy--ionone DM006942 N. A. Unclear 1 [7]
4-oxo--ionone DM006940 N. A. Oxidation - Auto-oxidation 2 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007554 Beta-ionone (+)-(S)-4-hydroxy--ionone Oxidation - 4S-hydroxylation CYP1A2 ... [7]
MR007556 Beta-ionone (?)-(R)-4-hydroxy--ionones Oxidation - 4-hydroxylation CYP1A2 [7]
MR007557 Beta-ionone 3-hydroxy--ionone Unclear CYP101B1 [7]
MR007555 (+)-(S)-4-hydroxy--ionone 4-oxo--ionone Oxidation - Auto-oxidation Unclear [7]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 101B1 (cyp101) DME1746 Novosphingobium aromaticivorans
Q2G637_NOVAD
1.14.15.1
[2] , [3]
Cytochrome P450 101C1 (cyp101) DME1747 Novosphingobium aromaticivorans
Q2G637_NOVAD
1.14.15.1
[2] , [4]
Cytochrome P450 109B1 (cyp109) DME1745 Bacillus anthracis
U5U1Z3_BACIU
1.14.14.1
[5] , [6]
Cytochrome P450 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[7]
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[7]
References
1 Beta-ionone-inhibited proliferation of breast cancer cells by inhibited COX-2 activity. Arch Toxicol. 2019 Oct;93(10):2993-3003.
2 Patients with primary biliary cirrhosis react against a ubiquitous xenobiotic-metabolizing bacterium. Hepatology. 2003 Nov;38(5):1250-7.
3 A cytochrome P450 class I electron transfer system from Novosphingobium aromaticivorans. Appl Microbiol Biotechnol. 2010 Mar;86(1):163-75.
4 Structural analysis of CYP101C1 from Novosphingobium aromaticivorans DSM12444. Chembiochem. 2011 Jan 3;12(1):88-99.
5 The crystal structure of the versatile cytochrome P450 enzyme CYP109B1 from Bacillus subtilis. Mol Biosyst. 2015 Mar;11(3):869-81.
6 The promises and risks of probiotic Bacillus species. Acta Biochim Pol. 2018 Dec 6;65(4):509-519.
7 In Vitro Regio- and Stereoselective Oxidation of -Ionone by Human Liver Microsomes

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